Tert-butoxy carbonyl dihydro artemisinin, preparation method and drug composition thereof

A technology of tert-butoxycarbonyl dihydroartemisinin and dihydroartemisinin, which is applied in the field of terpenoids, and can solve the problems that the solubility is not as good as artemether, and there is no in-depth research.

Inactive Publication Date: 2003-03-26
SHANGHAI INST OF MATERIA MEDICA CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

They are also highly active against malaria, but because they are less soluble in oil than artemether, they have not been studied in depth

Method used

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  • Tert-butoxy carbonyl dihydro artemisinin, preparation method and drug composition thereof

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specific Embodiment approach

[0041] The specific implementation of the present invention will be further elaborated below in conjunction with examples, but these examples are by no means any limitation to the present invention.

Synthetic example 1

[0043] First dihydroartemisinin (2.84 grams, 10 millimoles) was dissolved in 40 milliliters of dichloromethane, bis-tert-butyl dicarbonate (2.84 grams, 12.8 millimoles) was added, and then the acylation catalyst dimethylamino Pyridine (20 mg), stirred at room temperature. After the reaction was basically completed, the reaction solution was washed with water and dried with magnesium sulfate. The solvent was evaporated, and the obtained crude product was recrystallized with ethyl acetate-petroleum ether to obtain 3.00 g (yield 78%) of tert-butoxycarbonyl dihydroartemisinin (12-alpha body) and tert-butoxycarbonyl dihydroartemisinin Artemisinin (12-β body) 0.19 g (yield 5%).

Synthetic example 2

[0045] First, dihydroartemisinin (2.84 g, 10 mg) was dissolved in 50 ml of anhydrous acetonitrile, bis-tert-butyl dicarbonate (2.5 g, 11.3 mg) was added, and heated to reflux for reaction. After the reaction was basically completed, the solvent was evaporated from the reaction solution under reduced pressure, and the resulting crude product was separated by column chromatography (silica gel, 6% ethyl acetate / petroleum ether as eluent) to obtain tert-butoxycarbonyldihydroartemisinin ( 12-α body) 1.46 g (yield 38%) and tert-butoxycarbonyldihydroartemisinin (12-β body) 1.54 g (yield 40%).

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Abstract

The invention provides a tert-butoxycarbonyl dihydroartemisine, which is characterized by that said invention provides its structural formula, and it is made up by using dihydroartemisine as initiation raw material, and making it and double tertiary butyl dicarbonate implement acidation reactino in organic solvent. The invented mecicine composition for resisting parasitic disease contains tert-butoxycarbonyl dihydroartemisine with therapeutic effective dose and pharmaceutically-acceptable carrier. Said invented product is high in therapeutical effect and low in toxicity, can be used for preventing and curing the parasitic diseases of schistosomiasis and malaria, etc.

Description

technical field [0001] The invention relates to terpenoids, in particular to artemisinin derivatives, a preparation method thereof and an antiparasitic pharmaceutical composition containing the derivatives. Background technique [0002] According to the statistics of the World Health Organization, malaria is one of the most serious infectious diseases today. So far, more than 2 billion people live in malaria areas, and 500 million people suffer from malaria every year. Due to the resistance of malaria parasites to chloroquine, mechloroquine, halofantrine, quinine, and sulfonamide antimalarials, more than 2 million people die every year, half of whom are children. In 1972, Chinese researchers extracted artemisinin from the traditional Chinese medicine Artemisia annua L., and proved that it has a powerful antimalarial effect and can cure drug-resistant malaria. In order to improve its solubility and bioavailability, researchers at home and abroad have prepared various derivat...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K31/357A61P33/06C07D493/18
CPCY02A50/30
Inventor 李英王方道张瑜隋毅肖树华
Owner SHANGHAI INST OF MATERIA MEDICA CHINESE ACAD OF SCI
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